Sissy Transformation Party

May 26, 2017

The day I have been waiting for had finally arrived. Today was the day I would be transformed into a woman. My dominant girlfriend had the idea and enlisted a few of her friends to help out. My girlfriends instructions were specific.  I was to check into a hotel and wait for them to arrive. When they finally arrive, they were not empty handed each carrying a suitcase. Everyone was smiling and eager to begin.


My girlfriend ordered me to strip naked while they prepare for me.  As I got undressed, she took my clothes and put them into a plastic trash bag.   While this was going on, one of her friends was running a hot bubble bath for me. I was instructed to get in and make myself perfectly clean.  When I finished my bath and the tub emptied, my girlfriend enters with a pair of handcuffs and a paper bag.


She orders me to stand in the tub and place my hands above my head. She shackling me to the shower curtain bar, then took two bottles out of the bag and poured a pink lotion over me. My heart began to pound when I realized it was hair remover.

She covered me completely with the lotion, missing nothing from head to toe. She then told me she’d be back for me in few minutes, turned out the light and walked out. From the other room I could hear excited voices and the sound of glass containers being arranged on the tabletop and other unidentifiable noises.

About fifteen minutes later, my girlfriend came back and released me from my bonds and told me to rinse off the lotion. I rinsed off and rubbed body with a washcloth, removing any remaining body hair that remained. She looked me over carefully, then ordered me to the other room.

The other girls giggled when they saw me, but remained calm enough to go to work on me. I was escorted to a chair and the cuffs returned, shackling me to the arms of the chair. One of the girls began a pedicure, while another started applying false fingernails, shaping them and polishing them until my girlfriend, who was standing in the background giving instructions , was satisfied. The next phase of my transformation was the application of makeup. I was given a total makeover. When they were done, I amazed to say the least, I was a brand new person, I looked very feminine… at least from the neck up.

Now it was time to get dressed. After the cuffs were removed, I was helped into the very carefully chosen wardrobe they had for me laid out on the bed. One of the girls had to help me on with the corset, which had attached garters. Then she showed me how to put on the stockings without ruining them. While she fastened the snaps for me, another placed a bra around my chest and adjusted it to fit perfectly, then put a pair of realistic-looking falsies into the cups to fill it out. I was then given a mini dress to put on, which was a bit challenging to put on considered my chest and midsection were somewhat constricted. Once I had it on, I noticed it covered me well, The hem was pretty short and barely covered the nylons.

The final step was a long fiery red wig, which was carefully arranged in a feminine style and clipped to the only existing hair on my body. Now I looked totally feminine and felt it. My girlfriend had managed to locate a pair of high heels in my size to complete the outfit. I spent the next hour stumbling around the room learning to walk like a lady, much to the women’s amusement as they played cards while I practiced.

But the transformation was not yet complete, my girlfriend announced that it was time to get my ears pierced.  I thought she was joking and I would just wear some clips instead, but she was serious as she and the other girls brought me back to the chair.  One of the girls reminded me to cross my legs and sit like a lady while my girlfriend prepared to jab a needle into my earlobe.


When I was flinching because of the ice they used to try and numb my ear, My girlfriend suggested another option.  


“Look it is either right here right now or we take you across the street to the mall.” she said.


I never got the chance to make that decision as her girlfriends were totally into the new option.  So they stood me up and handed me a new purse and we walked out arm in arm to the mall.  I continued to struggle to walk in the high heels, but the long walk to the mall helped me get used to it.  We went inside and aside from a few curious stares and the odd hand on my ass, no one gave me second glance.

At the shop, my girlfriend spent a good deal of time picking out a nice pair of earrings for me, finally settling on a pair of gold ones. As I was sitting in the piercing chair, She leaned over and whispered something to the clerk.  The clerk then looked at me with a very unusual stare.  Examining me from head to toe.  I kept my legs pressed together as she paused around my secret region and my girlfriend reminded me to cross my legs.  The clerk finished her visual examination and gave me a sinister grin.  Before she started, she leaned forward and whispered to me.


“I will try not to hurt you, but please be very still.” she said.


When she was done, my girlfriend put the new earrings on.  I got up and looked in the mirror and the new addition really helped my ability to pass as a woman.  Before we left the clerk wanted to say one more thing to me.


“Are you going to be okay, Sweetie?” she asked.


I simply gave her a hug and said, “I’ll be fine, but thank you for asking.”

On the way back, my girlfriend said she forgot to get something and headed back in.  The other girls and I continued back to the hotel and waited for her. We got back to the hotel, but instead of heading to the room, we stopped at the restaurant.  We sat around laughing and talking about men, which I think was another way to embarrass me. It did, and I was blushing furiously no matter how I tried to hide it, which the girls found even more hilarious.

When my girlfriend came back a little while later, she had a big paper bag. As we started back up to the room, she told us that she asked the sales clerk if there was an adult store nearby.  The clerk suggested a boutique at the other end of the mall that was discreet and had just what she was looking for.  She then handed me the bag and my knees instantly buckled as I looked inside to find a huge strap on dildo complete with a harness and a big bottle of lube. I became terrified at the thought of having that giant cock rammed inside me. When I started to reject the idea, I was told that I would be punished later for talking back.

My girlfriend strapped on the dildo slowly, savoring each moment.  I was stripped of my dress and made to kneel down in front of  the chair my girlfriend was seated in.  I was then told it was time for my first blowjob. The other girls forced my head down over the big plastic dick and shouted tips and advice as my girlfriend laughed uncontrollably.


Then when my girlfriend decided enough was enough, she announced that it was time for my cherry to be popped. The other girls hooted their agreement and hauled me over to the bed. They bent me over and held me there, frightened and vulnerable. One of the girls sat on the back of my head while she parted my ass cheeks.  The other poured a good amount of the lubricant down the crack of my ass and rubbed it in, telling me that now I knew how a woman felt.  She inserted a finger into my hole to make sure I was completely ready, then sat back and let my girlfriend move in.

As I felt that big plastic dong begin to press against my opening, I groaned. The others giggled and encouraged my girlfriend on. Inch by inch, she forced the dildo into my ass, making me feel it deeper and deeper. The pain and humiliation were unbearable. When she had gotten the whole thing buried in me, she asked me how it felt to lose my cherry. All I could do was moan in pain. She laughed and told me the ride was only beginning.

She fucked me for a while, then switched with one of the other girls. Each had a chance to fuck me, and by the time the third had started, I no longer felt pain, only a numbing curious pleasure. My cock began to rise in spite of myself. The girls noticed this and did all they could to excite me further. After the last one had finished, my girlfriend told me that I wasn’t done yet.


After all, If the others could enjoy the taste of a man’s come, so why shouldn’t I do the same thing in my new role as a woman? She leaned down and slipped my rock hard cock into her warm mouth and sucked it, as much for the inevitable result as for all their appreciation. When I did come, she lovingly licked and sucked each drop from me, then leaned over my face.

One of the girls told me to open my mouth and stick out my tongue, which I did. My girlfriend spit my come out onto my tongue and watched as it dripped back into my mouth. She told me not to swallow it for one minute, so as to allow me the chance to savor the taste of sperm in my mouth. She and the others would make me stick out my tongue every ten seconds or so to check if the come was still there. When the longest minute of my life was up, I was allowed to swallow it. Then she said that she didn’t just want a girly boyfriend, but a sissy slave as well.

So they tied me to the bed and began to torture me to see how much I could take, and if I was worthy to be made a slave for my wonderful mistress. This went on for hours, and I drifted off to a special place between pain and pleasure. When they were done and had enough, I was released and told I was accepted as a slave. I was never so happy in my life as the four of us fell asleep together.

The next morning, as the other girls were leaving, my mistress/girlfriend told them not to forget about next Friday night. I was confused as I watched them get excited and began giggling and staring back at me with that similar sinister smile. My mistress turned to me and said, “Next Friday night, we are going to dress you again. Only next time, we are going out trolling to find you a real man to take care of.



  • Robertawana September 3, 2017 at 9:59 am

    MY panties are full of cum thks !!! Hott story wish I had a girlfriend like that

  • SuckMeFuckMe September 3, 2017 at 9:59 am

    Such a hot story,will be waiting eagerly for part 2.

  • EnjoyBoth September 3, 2017 at 2:25 pm

    A nice way to start }; )

  • iwish September 3, 2017 at 11:18 pm

    Nice Girlfriend

  • ThePhantom September 4, 2017 at 6:51 am

    Awaiting the next chapter..

  • TanyaRenee September 6, 2017 at 7:10 am

    can’t wait for the next story!!

  • subslv1 September 6, 2017 at 7:11 am

    Just like the start of one of my fantasies. Looking forward to the Next Friday Night Chapter.

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